Imagine this scenario. You make plans with your friends for a fun night in the city. You are out having a great time dancing, laughing – not a problem in the world. All of a sudden a familiar face from your past shows up and your mind goes into overdrive as you try to analyze the situation you are about to get yourself into. Just when you thought you were about to have that girls’ night out’, your Ex-Boyfriend shows up; you can’t resist and break your plans with your BFFS.

This is exactly what happened to me about a month ago.

I haven’t been with this guy a while now. It was a crazy up and down relationship during college that just never seemed to bring closure for either of us. He was my ‘comfort zone’ and whenever I wanted a little attention I knew that I could go to him and be satisfied in more ways than one, without feeling guilty the next morning.

So when my College Ex (all the way from Ohio, no less) showed up in New York, I was blindsided. Long story short, I remembered the last encounter with him and thought about how it lasted less than five minutes and was anything but satisfying. I decided it would be a bad idea to go back down a familiar path. It was time to start moving forward with my life. I thought to myself, “I don’t even want to be in a relationship with this guy and I am definitely not sitting here pining over him day and night like a pathetic love sick puppy.” But when it comes down to something like sex, that’s a whole different story.

“Ex-Sex is not necessarily a bad thing,” said John D. Moore, a well-known psychoanalyst and author of Confusing Love with Obsession: When Love Means Being in Control. “In fact, it can be wonderful,” he continued. “However, ‘Ex-Sex’ can become unhealthy if we feel the behaviors are preventing us from living to our full potential or blocking us from new experiences with others.”

I had a chance to speak with Moore and he gave me professional insight into this topic:

Moore says, “This is really a two-sided issue and each situation is different, so we can look at it from two different angles. When you encounter an ex boyfriend, especially when you don’t hate his guts, it’s hard not to think of the memories that linger in your head about the good times and bedroom romps throughout the relationship. And of course if the sex was mind-blowing, it is hard not to forget about it or constantly have the appetite to go back for seconds. But the real question to ask yourself is, Is it possible to just have casual sex with your Ex or is it just comfortable?”

When you are in a relationship with someone for so long, it’s hard to just stop caring. So is it really possible to casually be with someone when you still care about his feelings? Moore notes, “Physical connection can bring forth a flood of emotions in a woman, and when the compassion and feelings already exist, it can become a tidal wave overpowering thoughts before there’s a chance to escape. While you’re lying there with your ex lover, wrapped in his arms again, you can’t help but have the 12-second fantasy that you might get back together and start that life you had always spoke about. If you are having these thoughts, you have to ask yourself, is this really a casual encounter?”

One of the most memorable questions Moore raises, “If sex is happening frequently – is the person really an Ex?” Definitely something to think about, as are these questions:

1. Will engaging in sex with my Ex complicate our relationship further?
How will I feel about myself after sex? Will I be replicating any old patterns with my Ex?

2. Are the reasons for the original break-up still valid? If so – how might sex influence that decision?

3. Will sex with my Ex prevent me from having new relational experiences?
What does sex mean to me as a person?

By reflecting on our answers, we can discover what we really want and what the best decision would be. Moore believes that if a person is still going back to his or her Ex after many years, that the person is truly not an Ex. There is a relationship occurring at some level. And if so, both parties need to explore what they really want from each other and what healthy decision can be made to proceed.

So is there really such a thing as casual Ex-sex? Absolutely!

“Its all about how you can handle the situation and if in your gut you feel it can happen, and you can come out feeling no different than when you went in —then things are ok”. Moore’s opinion on the idea of casual Ex-sex was surprising and uplifting. “If casual means infrequent – then I do think there is such a thing,” he said. “If casual means, ‘accidental’ or ‘it just happened’ – I do not agree. People engage in sex with Exes for a variety of reasons. Some of these reasons can be nostalgic and for others because it is familiar. For many more however it is because ‘Ex-Sex’ can be hot! This happens when the emotional ties to the relationship have been either cut or lessened over the course of time. Ex-Sex traditionally tends to be more carnal in nature – more animalistic.”

But we must remember to take personal feelings into account before thinking we can engage in casual encounters with an Ex. If we’re not careful, what we think might be a beautiful thing could turn into a huge disaster.

Here’s one of the most important questions I asked Moore …Does sex with an Ex mean that we just can’t seem to let him go.

“If a woman (or a man for that matter) has a real difficult time living in the here and now because of previous hurts, then it may be helpful for the individual to seek up professional support from a therapist,” he said. “I am not sure any of us are capable of letting go of the past however, I do think it is possible to work through the past and find ways to bring meaning to those hurts in the here and now. This way, our past does not act as a barrier to achieving life goals”.

Its a simple question– can you and your former significant other really be just ‘friends with benefits’. But is sex ever simple? Especially when you throw someone you loved and were intimate with into the equation? So the next time you encounter your Ex, ask yourself, ‘Is it casual or just comfortable’? And, for once you may be able to make a complicated situation very simple.

If you’re interested in reading more from Moore, check out his book, Confusing Love with Obsession: When Love Means Being in Control. Available at Amazon.com.